The integration of wheels into luggage, suitcases, and other types of bags commonly used in travel has made such items much easier to transport by individual users. A person can now easily pull a piece of luggage through an airport, parking lot, or any other large area without having to lift the piece of luggage, and therefore the piece of luggage can be moved more easily be moved farther and faster than if the piece of luggage had no wheels. However, in order to move wheeled luggage, a user has to grasp a handle that is typically affixed to such luggage, thereby preventing that user from making use of one of their hands. In the modern travel environment, the amount of time a user may be required to transport his or her luggage has become greater than ever. Heightened security requires earlier arrival at airports and other transportation hubs and has introduced numerous and thorough security checkpoints and other obstacles between a traveler and his or her destination. To overcome such obstacles and increase the comfort of a traveler, the use of both hands, for example, to purchase a snack or retrieve documents required at a security checkpoint, is increasingly important. Thus, what is needed in the art is a device and methods to retain the convenience of using wheeled luggage while allowing a user full mobility and use of both hands.